St. Michaels Harbor Inn, Marina & Spa

Our welcoming staff will greet you and your guests as you arrive for your special day. Your ceremony, for up to 75 people, will be held on our covered port deck, overlooking St. Michaels Harbor. Your reception will be held in our Harbour Lights dining room, with floor to ceiling windows overlooking the same expansive views.
Our full service property offers you and your guests many amenities to make your event memorable. Located directly on St. Michaels Harbor, enjoy the water views as well as the ability to walk or bicycle throughout town. Enjoy a treatment at our spa or plan a kayak trip along the waterfront.

Our Award Winning Executive Chef and event team will work with you to plan a menu you would like to serve your guests. Every wedding is tailored to your exact preferences to reflect your personalities.

Point Pleasant

Exclusively yours…….Located just outside St. Michaels, Point Pleasant is a private peninsula with breathtaking 240° water views offering the perfect setting for intimate ceremonies and tented events.You will feel a world away at this private waterfront estate. Perfect for both intimate gatherings and large parties, historic Point Pleasant is a private, exclusive peninsula with serene water vistas. It is the perfect setting for the wedding of your dreams.

The peaceful great lawn overlooks Long Cove. Your wedding party will dress and prepare for the celebration in our Manor House. This inspiring, peaceful sanctuary will be exclusively yours. Together with our professional event planning team and award winning chef, you will create a magical day to be remembered forever. With no one around for miles, you will truly feel like this space exists just for your special occasion, ensuring your special day will be one your guests won't soon forget.

Tidewater Inn

Charm. Romance. Timeless elegance. The Tidewater Inn is located in picturesque town of Easton, Maryland. The Tidewater Inn allows you and your guests to savor the unique experience of an Eastern Shore destination wedding. The Inn has been lovingly restored to its historic splendor and offers beautiful indoor and outdoor settings for your special day. Also the perfect location for your rehearsal dinner, bridal tea or post wedding brunch. We also offer 87 tastefully appointed guests rooms featuring beautiful antique reproduction furnishings, premium linens and pillow top mattresses. Our dedicated staff works hard to make sure your needs and expectations are graciously met.

Prospect Bay

Prospect Bay is a hidden gem on the Eastern Shore, just minutes from the Chesapeake Bay Bridge, offering seating for up to 200 people. Featuring our expansive, beautiful grounds, full menu selection and a banquet facility large enough to accommodate all of your guests, Prospect Bay is fully equipped to make your event truly memorable. Our experienced, friendly staff will guide and assist you from the initial planning to the final toast. Call to arrange for a private tour!

Bartlett Pear Inn

Located in the heart of Historic Downtown Easton, Maryland, Bartlett Pear Inn offers a unique Wedding location. Small and quaint in size, but grand in urban feel and comfort, Bartlett Pear Inn can host a wedding of up to 80 guests.

Bartlett Pear Inn is an upscale American Bistro with a seven bedroom luxurious inn. The food's foundation is based on classic French technique with subtle touches of contemporary plate design. The Chef uses products from local farms whenever possible and values our region's drive for organic and sustainable practices. The restaurant is intended to be comfortable, fun and relaxing...a place to be seen.

The seven guest rooms - all named after pears - each have private bathrooms, many en suite, original wood floors, dramatic windows and front porch access. The innkeeping philosophy is outstanding and uncompromising. Bartlett Pear Inn welcomes all of their guests to celebrate the joy of food, dining and leisure with our friendly and professional staff.

The Milestone

Congratulations on your engagement! This is just the first step in starting your lives together. Planning the perfect wedding comes next. And, because you want nothing less than perfection you have come to The Milestone. Just as you commit to each other, we are committed to providing you with a wedding reception to remember.

At The Milestone, we take pleasure in helping you create your perfect wedding day. Our wedding specialists are ready to assist you with your plans and to suggest new ideas to design a wedding that is truly original. The Milestone's expert staff will provide assistance to ensure that all of your needs are satisfied, down to the smallest detail. Our staff of professionals guarantees a reception of world-class service and culinary excellence.

The Milestone is one of the largest special event venues on the Eastern Shore. We pride ourselves on attending to the specific needs of each guest by offering a range of menu options, inside and outside event choices, and flexible space that can be customized to meet any need. The Milestone is committed to making your wedding a special day that will live in your hearts forever.

Chesapeake Bay Maritime Museum

With its tranquil waterfront setting on Navy Point—overlooking the beautiful Miles River and beyond—the Chesapeake Bay Maritime Museum is a setting unlike any other. Several areas of the museum may be rented for wedding receptions, cocktail parties, and private events.

A nationally recognized institution dedicated to preserving the heritage of the Chesapeake, the Chesapeake Bay Maritime Museum brings the warm and casually elegant hospitality of the Eastern Shore of Maryland to each special occasion. Set on a private eighteen-acre campus with over 2,000 feet of waterfront in the village of St. Michaels, the Museum offers spectacular sunset views of the Miles, unique venues, and first-class event coordination to complement every occasion.

For information about hosting your special event in a unique setting, contact the Special Events Coordinator, Ida Heelan at 410-745-4944 or iheelan@cbmm.org

Dockside Express Cruises & Tours

Located in Tilghman’s Island, let us take you for a cruise on the 50 foot, 49 passenger USCG-inspected EXPRESS ROYALE. Available for rehearsal dinners, romantic sunset cruises, crab feasts, and more! For your daytime activities, we offer scavenger hunts, crabbing parties and eco-tours. We can do a sit down meal for up to 28 people, small weddings on board for up to 30 guests, drinks and hors d’oeurves for up to 49 guests. We offer a full catering menu and a full premium bar. Charters can depart from Tilghman’s Island, Kent Island, Easton, St. Michaels or Oxford.

The Inn at Perry Cabin

The Chesapeake Bay's Most Exclusive Wedding Destination

Awash in stark whites and navy blue, the Inn at Perry Cabin is a throwback to the Chesapeake's finest retreat for your destination wedding, complete with weathered dock and picturesque gazebo. Guests laze away the afternoon in Adirondacks and celebrate matrimony on the estate's waterfront lawn, as sailboats glide along the Miles River.

Select from one of the Inn's four customizable packages to make your wedding as idyllic as Perry Cabin's scenic setting. For you and your loved ones, the Inn offers 78 generously appointed rooms, unparalleled dining and the indulgent full-service Linden Spa. The well-manicured botanical gardens provide a sensory experience all its own, for the ultimate in outdoor dining and celebrations. Blue and pink hydrangeas frame large windows while bayberry's spicy scent lingers well into your evening.

The town of St. Michaels is the epitome of Maryland's Eastern Shore. The Inn at Perry Cabin is the ultimate indulgence in romance and luxury for your destination wedding. Experience the historic elegance and sophistication of the Chesapeake Bay's most magnificent mansion as host of your breathtaking day.

Brittland Estates

Historic mansions, river vistas and forever fields, the world of Brittland personifies elegance in a rural setting. Embracing a collection of heritage properties, near Chestertown on Maryland's Eastern Shore, Brittland Estates gives the discerning bride a series of settings and moods to create her distinctive celebration. The bride rents an estate for a minimum of 2 nights. Brittland Estates gives individualized tours 7 days a week, please call to make an appointment.

Harbourtowne Golf Resort and Conference Center

Dream Your Perfect Waterfront Experience

At Harbourtowne we make those dreams a reality. Harbourtowne is the premier destination for a romantic wedding on the shores of the Chesapeake Bay. Imagine the perfect backdrop for a sunset ceremony or an afternoon reception on our Bayside Deck. We understand that each wedding is a unique and personal event and should be a worry-free and memorable experience. Our full-time, on-site wedding coordinator will take you step-by-step through the details that make your day special from the rehearsal dinner to the ceremony and finally the reception. And, since Harbourtowne has a policy of one wedding per day, you'll receive the personal attention you deserve to ensure everything goes as planned, at a price that is truly affordable.

When you reserve and plan your wedding with Harbourtowne, we include the opportunity to reserve the building of guest rooms just in front of the ceremony area. This offers privacy to the bride and groom, and family and friends, and each room has a gorgeous waterfront view of the Chesapeake Bay. Before or after the wedding, your friends and family can enjoy a full weekend of events—a golf outing at our on-site course, rent a bike and tour the resort and St. Michaels, or just lounge by the pool.

To begin planning today, call Elaine Phillips at (800) 446-9066 or send an email, ephillips@harbourtowne.com.

The Historical Society of Talbot County

The Historical Society of Talbot County invites you to make history part of your event.

The Auditorium is housed in the former Ebenezer Methodist Episcopal Church, built circa 1856. The original stained-glass windows and ornate plaster ceiling create a uniquely appealing atmosphere in the versatile, multi-purpose facility. Recipient of the 1988 Maryland Historical Trust Preservation Award and a nominee for the A.S.I.D. Thomas Jefferson Award, architects and preservationists have hailed the modernized and renovated Auditorium.

The facility includes: stage, audiovisual equipment, a full-service kitchen, optional dance floor, balcony overlooking the main room, 1,710 square feet of pillar-free floor, controlled lighting, wheelchair accessible (via elevator), air-conditioned, reasonable rental rates. The building is available for use by individuals, community groups, corporations and non-profit groups, providing a charming and historic atmosphere for meetings, parties, weddings, receptions, and other events. Rental rates vary.

The building is available for use by individuals, community groups, corporations and non-profit groups, providing a charming and historic atmosphere for meetings, parties, weddings, receptions, and other events. Rental rates vary.

In addition to our auditorium, the HSTC gardens are a verdant oasis located in historic downtown Easton. They are the perfect setting for a small wedding, reception or social gathering. There is minimal lighting available for evening events. Electricity is available in the gardens. Rental rates & fees vary.

Patriot Cruises

Located in St. Michaels harbor, this venue is perfect for a true Eastern Shore wedding, rehearsal dinner, or rehearsal cocktail party for your guests. Our Captain can marry you on the bow or under the canopy while you cruise upon the beautiful Miles River. The Patriot is a 2 level 149 passenger cruise boat with the main deck fully air conditioned and the top deck partially covered by a canopy.

We team with the top caterers and restaurants in Talbot County to provide outstanding food for your event. We have an extensive list of beer, wine and mixed drinks but can also special order for your event.

To enhance your destination wedding, we invite your wedding guests to join one of our historic narrated public cruises. Relax aboard the Patriot while learning about our local beginnings, view historic homes and wildlife and watch local watermen harvest clams, oysters and the famous Chesapeake Bay Blue Crab during their respective seasons. With an advanced reservation, we can offer special group rate pricing.

The Oaks - Waterfront Inn and Events

The Oaks is an elegant yet comfortable 240 year old plantation house situated on the banks of Oak Creek in Royal Oak, Maryland. The Main House is just steps from the waterside and has fourteen guest rooms and a private Bridal Cottage, and a scenic waterfront view. Your wedding ceremony can overlook the water, and then move onto our spacious covered dock for cocktail hour only to be followed by a fabulous reception in our exquisite new grand ballroom.

Relax and enjoy your friends and family at The Oaks. The entire inn, both grounds and staff, will be devoted exclusively to your occasion. We offer many activities for your guests to enjoy such as canoeing, bicycling, swimming, shuffleboard, horseshoes and a putting green.

The Oaks staff takes great pride in creating the perfect atmosphere for your wedding. We work closely with each couple to tailor every aspect of the event to their own unique personalities. Our award winning chef will prepare a unforgettable dining experience that will be a highlight of the weekend.

Please call us to schedule a time to visit The Oaks so that we can show you our property and discuss the details of your event.